Abstract
Zinc chloride-catalyzed double debromoalkoxylation of (dibromomethyl)arenes on treatment with trialkyl orthoformates resulted in the corresponding aromatic aldehyde acetals. On the first step, α-brominated ether is formed, which undergoes the second debromoalkoxylation producing acetal. This method is tolerated to ester functionalized derivatives.
Similar content being viewed by others
References
Weygand-Hilgetag, Organisch-chemische Experimentierkunst, J. A. Barth, Leipzig, 1964, 1142 pp.
D. Barton, W. D. Ollis, Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds, Vol. 1, Stereochemistry, Hydrocarbons, Halo Compounds, Oxygen Compounds, Ed. J. F. Stoddart, Pergamon Press, Oxford—New York—Toronto—Sydney—Paris—Frankfurt, 1979.
J. March, Advanced Organic Chemistry. Reactions, Mechanisms and Structure, John Wiley and Sons, New York, 1992, 387 pp.
L. A. Yanovskaya, S. S. Yufit, V. F. Kucherov, Khimiya atsetalei [Chemistry of Acetals], Nauka, Moscow, 1975, 273 pp. (in Russian).
R. B. Moffett, Org. Synth., 1963, Coll. Vol. 4, 427.
K. Schank, Chem. Ber., 1967, 100, 2292.
G. Cavallini, J. Med. Chem., 1964, 7, 255; DOI: 10.1021/jm00333a003.
A. Clerici, N. Pastori, O. Porta, Tetrahedron, 1998, 54, 15679; DOI: 10.1016/S0040-4020(98)00982-X.
H. Nao, K. Kiyoshi, S. Tsuneo, S. Hisashi, Synlett, 2004, 1074; DOI: 10.1055/s-2004-820038.
C. Wiles, P. Watts, S. J. Haswell, Tetrahedron, 2005, 61, 5209; DOI: 10.1016/j.tet.2005.03.082.
W. Ehrlichmann, K. Friedrich, Chem. Ber., 1961, 94, 2217.
E. Schmitz, Chem. Ber., 1958, 91, 410.
I. T. Crosby, G. A. Pietersz, J. A. Ripper, Aust. J. Chem, 2008, 61, 138; DOI: 10.1071/CH07404.
G. V. Kryshtal, G. M. Zhdankina, E. P. Serebryakov, Russ. Chem. Bull., 1993, 42, 866.
M. B. Gazizov, K. M. Gazizov, M. A. Pudovik, A. A. Mukhamadiev, R. F. Karimova, A. I. Sadykova, O. G. Sinyashin, Dokl. Chem., 2001, 381, 321.
M. B. Gazizov, M. A. Pudovik, K. M. Gazizov, R. F. Karimova, R. A. Khairullin, A. S. Romakhin, V. V. Nikitin, J. Gen. Chem., 2002, 72, 1488.
M. B. Gazizov, S. Yu. Ivanova, R. F. Karimova, L. R. Bagauva, K. S. Gazizova, A. A. Karimova, Russ. Chem. Bull., 2016, 65, 191.
M. B. Gazizov, S. Yu. Ivanova, L. R. Bagauva, R. A. Khairullin, R. Z. Musin, Tetrahedron Lett., 2016, 57, 210; DOI: org/10.1016/j.tetlet.2015.12.005.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1230—1233, July, 2017.
Rights and permissions
About this article
Cite this article
Gazizov, M.B., Ivanova, S.Y., Bashkirtseva, N.Y. et al. Synthesis of aromatic aldehyde acetals from (dibromomethyl)arenes. Russ Chem Bull 66, 1230–1233 (2017). https://doi.org/10.1007/s11172-017-1877-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-017-1877-6